I have a FreeBSD machine running OpenBSD's SPAMd and SPAMd crashes sometimes... "/usr/local/etc/rc.d/obspamd status" show the process is not running and there is only a gap in my logs... nothing about the failure. Restarting the service works.

Any ideas?

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Yes, the problem is also very obscure to me. What makes me guess it's a crash is the absence of anything useful in my log file. I simply have a "gap" between the time the process died and when I restarted it manually:

Please note the patch change only the binary name to obspamd and adjusts the name in the rc script and for the pitfile.
If the problem persists we have to search for the reason in the ported spamd.
If the problem is gone we have to search if something send a signal to the wrong deamon.
I hope the second one

I could sleep late this morning because there were no Nagios alarms to wake me up

Thats one of the reason why people choose *BSD

I'm a little afread that this happens again if you update the mail/spamd port.

I have taken a short look into the community from cPanel and notice that some of them adjust there scripts from `pkill -HUP $procname` to 'kill -HUP `cat /var/run/xxx.pid`'

Can you do a grep -R spamd over the cPanel scripts?
Maybe they can adjust the kill command in the next release to the pidfile?

At the moment there are two pid files
/var/run/spamd/spamd.pid => SpamAssassin spamd
/var/run/spamd.pid => OpenBSD spamd (in your case with patch now obspamd.pid)

Reasons to not change the default deamon name to obspamd for me
- keep code and names from OpenBSD so people know it comes from there
- break of existing scripts for the mail/spamd port since procname change, for example logfile parsers, statistics ...
- bad feedback for the change from pf-spamd to obspamd (that's another story)